Synthesis of (+)-discodermolide and analogues by control of asymmetric induction in aldol reactions of γ-chiral (Z)-enals

Ian Paterson; Gordon John Florence

doi:10.1016/S0040-4039(00)01165-5

Synthesis of (+)-discodermolide and analogues by control of asymmetric induction in aldol reactions of γ-chiral (Z)-enals

Research output: Contribution to journal › Article › peer-review

Abstract

The boron-mediated aldol reactions of the (Z)-enals 3 and 7 proceed with high levels of 1,4-stereo-induction arising from the gamma-substituent. Reagent control from (+)-Ipc(2)BCl can be used effectively to overturn this substrate bias, thus enabling the stereocontrolled formation of (+)-discodermolide (1) and related analogues 15-18. (C) 2000 Elsevier Science Ltd. All rights reserved.

Original language	English
Pages (from-to)	6935-6939
Number of pages	5
Journal	Tetrahedron Letters
Volume	41
Issue number	35
DOIs	https://doi.org/10.1016/S0040-4039(00)01165-5
Publication status	Published - 26 Aug 2000

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Keywords

discodermolide
boron aldol
isopinocampheyl
anticancer
remote stereoinduction
SPONGISTATIN-1 ALTOHYRTIN-A
MARINE MACROLIDE SYNTHESIS
STEREOCONTROLLED SYNTHESIS
METHYL KETONES
AGENT
(-)-DISCODERMOLIDE
DISCODERMOLIDE
PACLITAXEL
BINDING
CELLS

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@article{bf9cf51cddc74135bb396d3ffc13bc68,

title = "Synthesis of (+)-discodermolide and analogues by control of asymmetric induction in aldol reactions of γ-chiral (Z)-enals",

abstract = "The boron-mediated aldol reactions of the (Z)-enals 3 and 7 proceed with high levels of 1,4-stereo-induction arising from the gamma-substituent. Reagent control from (+)-Ipc(2)BCl can be used effectively to overturn this substrate bias, thus enabling the stereocontrolled formation of (+)-discodermolide (1) and related analogues 15-18. (C) 2000 Elsevier Science Ltd. All rights reserved.",

keywords = "discodermolide, boron aldol, isopinocampheyl, anticancer, remote stereoinduction, SPONGISTATIN-1 ALTOHYRTIN-A, MARINE MACROLIDE SYNTHESIS, STEREOCONTROLLED SYNTHESIS, METHYL KETONES, AGENT, (-)-DISCODERMOLIDE, DISCODERMOLIDE, PACLITAXEL, BINDING, CELLS",

author = "Ian Paterson and Florence, \{Gordon John\}",

year = "2000",

month = aug,

day = "26",

doi = "10.1016/S0040-4039(00)01165-5",

language = "English",

volume = "41",

pages = "6935--6939",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier",

number = "35",

}

TY - JOUR

T1 - Synthesis of (+)-discodermolide and analogues by control of asymmetric induction in aldol reactions of γ-chiral (Z)-enals

AU - Paterson, Ian

AU - Florence, Gordon John

PY - 2000/8/26

Y1 - 2000/8/26

N2 - The boron-mediated aldol reactions of the (Z)-enals 3 and 7 proceed with high levels of 1,4-stereo-induction arising from the gamma-substituent. Reagent control from (+)-Ipc(2)BCl can be used effectively to overturn this substrate bias, thus enabling the stereocontrolled formation of (+)-discodermolide (1) and related analogues 15-18. (C) 2000 Elsevier Science Ltd. All rights reserved.

AB - The boron-mediated aldol reactions of the (Z)-enals 3 and 7 proceed with high levels of 1,4-stereo-induction arising from the gamma-substituent. Reagent control from (+)-Ipc(2)BCl can be used effectively to overturn this substrate bias, thus enabling the stereocontrolled formation of (+)-discodermolide (1) and related analogues 15-18. (C) 2000 Elsevier Science Ltd. All rights reserved.

KW - discodermolide

KW - boron aldol

KW - isopinocampheyl

KW - anticancer

KW - remote stereoinduction

KW - SPONGISTATIN-1 ALTOHYRTIN-A

KW - MARINE MACROLIDE SYNTHESIS

KW - STEREOCONTROLLED SYNTHESIS

KW - METHYL KETONES

KW - AGENT

KW - (-)-DISCODERMOLIDE

KW - DISCODERMOLIDE

KW - PACLITAXEL

KW - BINDING

KW - CELLS

UR - https://www.scopus.com/pages/publications/0034718386

UR - http://www.sciencedirect.com/science?_ob=ArticleURL&_udi=B6THS-410KMJB-1S&_coverDate=08%2F31%2F2000&_alid=444789330&_rdoc=1&_fmt=&_orig=search&_qd=1&_cdi=5290&_sort=d&view=c&_acct=C000050221&_version=1&_urlVersion=0&_userid=10&md5=1cdb66016748c032cf8e8e43ee7604b1

U2 - 10.1016/S0040-4039(00)01165-5

DO - 10.1016/S0040-4039(00)01165-5

M3 - Article

SN - 0040-4039

VL - 41

SP - 6935

EP - 6939

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 35

ER -

Synthesis of (+)-discodermolide and analogues by control of asymmetric induction in aldol reactions of γ-chiral (Z)-enals

Abstract

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Keywords

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